Dimethylformamide → 4-Cyclobutylbenzaldehyde

HRID 19766Notes

Reaction equation

HRID 19766 reaction equation
[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Br[C:13]1C=CC(C2CCC2)=CC=1.[Li]CCCC.CCCCCC.CN(C=O)C>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=2)[CH2:3][CH2:2][CH2:13]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 115064744-CyclopropylbenzaldehydeHCID 571850921-Bromo-4-cyclobutylbenzeneHCID 178418339Butyllithium

Product 1

HCID 571743534-CyclobutylbenzaldehydeYield 67%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S1-A) using 830 mg of 1-bromo-4-cyclobutyl-benzene (3.93 mmol), 2.7 ml of a 1.6 molar solution of n-BuLi in hexane (4.32 mmol) and 605 μl of DMF (7.86 mmol). The isolated residue was purified by flash column chromatography (5:95 EtOAc/cyclohexane) to give 422 mg of 4-cyclobutyl-benzaldehyde (67%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.89 (m, 1H), 1.97-2.26 (m, 3H), 2.40 (m, 2H), 3.63 (quint, J=8.5 Hz, 1H), 7.36 (d, J=8.0 Hz, 2H), 7.81 (d, J=8.0 Hz, 2H), 9.97 (s, 1H).

Workup

  1. customThe isolated residue was purified by flash column chromatography (5:95 EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-aad95bf5e23a4e0090f31c175cafb232
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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